Forming clear, wettable silicone hydrogel articles without surface treatments

• US 20100280146A1
• Filed: 03/05/2004
• Published: 11/04/2010
• Est. Priority Date: 09/06/2002
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: McCabe, Kevin P., Vanderlaan, Douglas C., Petisce, James R., Alli, Azaam
• Granted Patent: US 8,158,695 B2
• Time in Patent Office: Days
• US Class Current: 523/107
• CPC Class Codes: A61L 2430/16 for reconstruction of eye parts, e.g. intraocular lens, cornea
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 27/26 Mixtures of macromolecular compounds
• CPC Class Codes: A61L 27/52 Hydrogels or hydrocolloids
• CPC Class Codes: C08L 83/04 Polysiloxanes

Abstract

The present invention is a composition, which may be used to form contact lenses, comprising at least one silicone containing component, at least one hydrophilic component, at least one high molecular weight hydrophilic polymer and at least one diluent with an alpha value of about 0.5 to about 1 and a Hansen solubility parameter of less than about 10.

Claims

1. A composition comprising:

at least one silicone containing component,

at least one hydrophilic component,

at least one high molecular weight hydrophilic polymer, and

at least one diluent having an alpha value of between about 0.05 and about 1 and a Hansen solubility parameter, δ

p, of less than about 10, wherein the composition forms a clear blend at a selected reaction temperature, wherein the reaction temperature is up to about 75 C.

2. The composition of claim 1 further comprising at least one silicone containing compatibilizing component in an amount insufficient to compatibilize the blend absent the diluent.

3. The composition of claim 1 wherein the alpha value is between about 0.1 and about 0.9.

4. The composition of claim 1 wherein the hydrophilic component and the silicone containing component are polymerizable and the composition forms a clear article when polymerized at the reaction temperature.

5. The composition of claim 1 wherein the diluent is selected from the group consisting of alcohols having at least three carbon atoms.

6. The composition of claim 1 wherein the diluent is selected from the group consisting of alcohols having at least four carbon atoms.

7. The composition of claim 1 wherein the diluent is selected from the group consisting of alcohols having at least six carbon atoms.

8. The composition of claim 1 wherein the δ

p of less than about 6.

9. The composition of claim 1 wherein the silicone containing compatibilizing component is present in an amount between about 0 and about 5 weight % of the composition.

10. The composition of claim 1 wherein diluent is one or more selected from the group consisting of 1-ethoxy-2-propanol, diisopropylaminoethanol, isopropanol, 3,7-dimethyl-3-octanol, 1-decanol, 1-dodecanol, 1-octanol, 1-pentanol, 2-pentanol, 1-hexanol, 2-hexanol, 2-octanol, 3-methyl-3-pentanol, tert-amyl alcohol, tert-butanol, 2-butanol, 1-butanol, 2-methyl-2-pentanol, 2-propanol, 1-propanol, ethanol, 2-ethyl-1-butanol, SiGMA acetate, 1-tert-butoxy-2-propanol, 3,3-dimethyl-2-butanol, tert-butoxyethanol, 2-octyl-1-dodecanol, decanoic acid, octanoic acid, dodecanoic acid, 2-(diisopropylamino)ethanol and mixtures thereof.

11. The composition of claim 1 wherein the diluent is one or more selected from the group consisting of 3,7-dimethyl-3-octanol, 1-dodecanol, 1-decanol, 1-octanol, 1-pentanol, 1-hexanol, 2-hexanol, 2-octanol, 3-methyl-3-pentanol, 2-pentanol, t-amyl alcohol, tert-butanol, 2-butanol, 1-butanol, 2-methyl-2-pentanol, 2-ethyl-1-butanol, ethanol, 3,3-dimethyl-2-butanol, 2-octyl-1-dodecanol, decanoic acid, octanoic acid, dodecanoic acid and mixtures thereof.

12. The composition of claim 1 wherein the diluent is one or more selected from the group consisting of 3,7-dimethyl-3-octanol, 1-dodecanol, 1-decanol, 1-octanol, 1-pentanol, 1-hexanol, 2-hexanol, 2-octanol, 1-dodecanol, 3-methyl-3-pentanol, 1-pentanol, 2-pentanol, t-amyl alcohol, tert-butanol, 2-butanol, 1-butanol, 2-methyl-2-pentanol, 2-ethyl-1-butanol, 3,3-dimethyl-2-butanol, 2-octyl-1-dodecanol and mixtures thereof.

13. The composition of claim 1 wherein the high molecular weight hydrophilic polymer has a molecular weight greater than about 150,000 Daltons.

14. The composition of claim 1 wherein the high molecular weight hydrophilic polymer has a molecular weight between about 150,000 to about 2,000,000 Daltons.

15. The composition of claim 1 wherein the high molecular weight hydrophilic polymer has a molecular weight between about 500,000 to about 1,500,000 Daltons.

16. The composition of claim 1 wherein the high molecular weight hydrophilic polymer is present in an amount between about 1 to about 15 weight % of the composition.

17. The composition of claim 1 wherein the high molecular weight hydrophilic polymer is present in an amount between about 3 to about 12 weight % of the composition.

18. The composition of claim 1 wherein the high molecular weight hydrophilic polymer comprises a cyclic amide in a backbone of the high molecular weight hydrophilic polymer.

19. The composition of claim 1 wherein the high molecular weight hydrophilic polymer comprises a cyclic imide in a backbone of the high molecular weight hydrophilic polymer.

20. The composition of claim 1 wherein the high molecular weight hydrophilic polymers is one or more selected from the group consisting of poly-N-vinyl pyrrolidone, poly-N-vinyl-2-piperidone, poly-N-vinyl-2-caprolactam, poly-N-vinyl-3-methyl-2-caprolactam, poly-N-vinyl-3-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-caprolactam, poly-N-vinyl-3-ethyl-2-pyrrolidone, and poly-N-vinyl-4,5-dimethyl-2-pyrrolidone, polyvinylimidazole, poly-N—

N-dimethylacrylamide, polyvinyl alcohol, polyacrylic acid, polyethylene oxide, poly 2 ethyl oxazoline, heparin polysaccharides, polysaccharides, and mixtures, block copolymers, random copolymers, branched copolymers, multichain copolymers, comb-shaped copolymers, and star shaped copolymers thereof.

21. The composition of claim 1 wherein the high molecular weight hydrophilic polymer comprises poly-N-vinylpyrrolidone.

22. The composition of claim 1 wherein the reaction temperature is about 40°

C.

23. The composition of claim 1 wherein a ratio of moles HBD:

moles HBA (HMWHP) is ≧

about 0.8 for the composition.

24. The composition of claim 1 wherein a ratio of moles HBD present to moles HBD preferred is ≧

about 0.6 for the composition.

25. The composition of claim 1 wherein a ratio of HTS is >

about 0.14 for the composition.

26. A composition comprising

at least one silicone containing component,

at least one hydroxyl containing component,

at least one high molecular weight hydrophilic polymer, and

at least one diluent having an alpha value of between about 0.05 and about 1 and a Hansen solubility parameter, δ

p, of less than about 10, wherein the composition forms a clear blend at a selected reaction temperature, wherein the reaction temperature is up to about 75°

C.

27. The composition of claim 26 further comprising at least one silicone containing compatibilizing component in an amount insufficient to compatibilize the blend absent the diluent.

28. The composition of claim 26 wherein the hydroxyl containing component comprises at least one polymerizable double bond and at least one hydrophilic functional group.

29. The composition of claim 28 wherein the polymerizable double bond is one or more selected from the group consisting of acrylic, methacrylic, acrylamido, methacrylamido, fumaric, maleic, styryl, isopropenylphenyl, O-vinylcarbonate, O-vinylcarbamate, allylic, O-vinylacetyl and N-vinyllactam and N-vinylamido double bonds.

30. The composition of claim 26 wherein the hydroxyl containing component is one or more selected from the group consisting of 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylamide, 2-hydroxyethyl acrylamide, 2-hydroxyethyl vinyl carbamate, 2-hydroxyethyl vinyl carbonate, 2-hydroxypropyl methacrylate, hydroxyhexyl methacrylate, hydroxyoctyl methacrylate and mixtures thereof.

31. The composition of claim 26 wherein the hydroxyl containing component comprises 2-hydroxyethyl methacrylate.

32. The composition of claim 26 wherein the silicone containing component comprises a fluoroether-siloxane-methacrylate macromer.

33. The composition of claim 28 or 32 wherein the hydroxyl containing component comprises 2-hydroxyethyl methacrylate and

the high molecular weight hydrophilic polymer comprises poly-N-vinylpyrrolidone.

34. The composition of claim 28 wherein the silicone containing component comprises monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane.

35. The composition of claim 34 wherein the hydroxyl containing component comprises 2-hydroxyethyl methacrylate and the high molecular weight hydrophilic polymer comprises poly-N-vinylpyrrolidone.

36. The composition of claim 26 wherein the reaction temperature is about 40°

C.

37. A composition comprising

a silicone containing component,

a hydrophilic component,

a high molecular weight hydrophilic polymer and

a diluent, wherein the weight ratio of the silicone containing component:

the hydrophilic component;

the high molecular weight hydrophilic polymer;

the diluent is about 1;

about 1.6;

about 0.3;

about 2 and the composition is a compatible mixture at about room temperature.

38. The composition of claim 37 wherein the hydrophilic component comprises

DMA,

the silicone containing component comprises monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane, and

the high molecular weight hydrophilic polymer comprises PVP.

39. An ophthalmic device comprising a cured compound, wherein the compound in precure form comprises

at least one silicone containing component,

at least one hydrophilic component,

at least one high molecular weight hydrophilic polymer, and

at least one diluent having an alpha value of between about 0.05 and about 1 and a Hansen solubility parameter, δ

p, of less than about 10.

40. An ophthalmic device comprising a cured compound, wherein the compound in precure form comprises

at least one silicone containing component,

at least one hydroxyl containing component,

at least high molecular weight hydrophilic polymer, and

at least one diluent having an alpha value of between about 0.05 and about 1 and a Hansen solubility parameter, δ

p, of less than about 10.

41. A method of making a clear and wettable ophthalmic device comprising

Combining at least one silicone containing component, at least one hydrophilic component, at least one high molecular weight hydrophilic polymer, and at least one diluent having an alpha value of between about 0.05 and about 1 and a Hansen solubility parameter, δ

p, of less than about 10,

Placing the combination in a mold,

Curing the combination,

Extracting the combination from the mold, and

Removing substantially all of the diluent from the combination.

42. A method of making a clear and wettable ophthalmic device comprising

Combining at least one silicone containing component, at least one hydroxyl containing component, at least one high molecular weight hydrophilic polymer, and at least one diluent having an alpha value of between about 0.05 and about 1 and a Hansen solubility parameter, δ

p, of less than about 10,

Placing the combination in a mold,

Curing the combination, and

Extracting the combination from the mold.

43. A composition comprising

monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane;

N,N-dimethylacrylamide;

2-hydroxyethyl methacrylate;

tetraethyleneglycol dimethacrylate;

poly(N-vinyl pyrrolidone) (K value

     90);

bis(2,4,6-trimethylbenzoyl)-phenyl phosphine oxide; and

3,7-dimethyl-3-octanol.

44. A composition comprising:

monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane;

N,N-dimethylacrylamide;

2-hydroxyethyl methacrylate;

ethylene glycol dimethacrylate;

2-(2′

-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole;

poly(N-vinyl pyrrolidone) (K value

     90);

bis(2,4,6-trimethylbenzoyl)-phenyl phosphine oxide; and

t-amyl alcohol.